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33846432658
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Carbocyclic Three-Membered Ring Compounds, In Houben-Weyl, E 17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
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(c) Carbocyclic Three-Membered Ring Compounds, In Houben-Weyl, Vol. E 17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1996.
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6
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(b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Green Chem. 2003, 5, 85.
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Shao, L.-X.; Huang, J.-W.; Shi, M. Tetrahedron 2004, 60, 11895.
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Chen, W.-L.; Huang, X.; Zhou, H.-W.; Ren, L.-J. Synthesis 2006, 609.
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19
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33846412882
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General Procedure for the Reaction of 1,1-Diphenyl- methylenecyclopropane (1a) with 1,3-Cyclohexadione (2a) in the Presence of Sn(OTf)2. 1,1-Diphenylmethylenecyclopropane (1a, 0.30 mmol, 1,3-cyclohexadione (2a, 0.30 mmol) and Sn(OTf)2 (0.03 mmol) were dissolved in 2.0 mL of DCE. The reaction mixture was stirred at 85 °C for 4 h. Then, the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding homoallylic alcohol product 3a in 82% yield. 3-(4,4-Diphenylbut-3-enyloxy)cyclohex-2-enone (3a, Colorless solid, mp 78-79 °C. IR (CH2CU, v, 3051, 3024, 2945, 2886, 1655, 1604, 1493, 1397, 1366, 1349, 1328, 1219, 1183, 1153, 1014, 761, 701 cm-1. 1H NMR (300 MHz, CDCl3, TMS, δ, 1.93-2.01 (2 H, m, CH2, 2.34 (2 H, t, J, 6.6 Hz, CH2, 2.41 2 H, t, J, 6.6
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2: C, 82.99; H, 6.96%. Found: C, 82.83; H, 7.01%.
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20
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0141741420
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For some other selected papers on the Lewis acid catalyzed reactions of MCPs, see: a
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For some other selected papers on the Lewis acid catalyzed reactions of MCPs, see: (a) Shi, M.; Shao, L.-X.; Xu, B. Org. Lett. 2003, 5, 579.
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